1-(Bromomethyl)-3-(trifluoromethyl)benzene → 3-iodo-4-nitro-1-(3-(trifluoromethyl)benzyl)-1H-indazole

Participants

Reaction Conditions

Reaction Steps

To a slurry of 3-iodo-4-nitro-1H-indazole (0.410 g, 1.42 mmol) and CH3CN (7.0 mL) was added 1-(bromomethyl)-3-(trifluoromethyl)benzene (0.261 mL, 1.70 mmol) and the solution was cooled to 0° C. 2-tert-Butyl-1,1,3,3-tetramethylguanidine (0.372 mL, 1.84 mmol) was added and the mixture was gradually warmed to ambient temperature where it stirred for 2 hours. The mixture was concentrated and diluted with saturated aqueous NH4Cl (20 mL) and EtOAc (75 mL). The layers were mixed and separated and the organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The crude product was passed through a silica gel plug eluting with 20% EtOAc/hexane to provide 0.542 g (85%) of the product as dark yellow/orange oil.

Provenance & Evidence